


Love Quest [Knight!Dean x Princess!Reader]

by whitehopper



Series: Dean Winchester x Reader [2]
Category: Supernatural
Genre: AU, Alternate Universe, Alternate Universe - Medieval, F/M, Knight, Princess - Freeform
Language: English
Status: In-Progress
Published: 2018-04-03
Updated: 2018-04-03
Packaged: 2019-04-17 23:00:23
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,109
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14199525
Author URL: https://archiveofourown.org/users/whitehopper/pseuds/whitehopper
Summary: In the midst of facing a threat of war, your father, the king, sends you away from the kingdom in fear of your safety. Angry, offended, and wanting to help, you challenge your father’s request, claiming that “for your safety” was a pathetic excuse. The frustrated king, in no mood to deal with your antics, tells you that you must find a prince worthy of your hand with the help of your trusty knight, Dean Winchester. Your father never expected you to actually follow through with his request; and neither did you.-I'm really bad with summaries lol





	Love Quest [Knight!Dean x Princess!Reader]

**Author's Note:**

> Just a series I came up with over break. I hope you enjoy my first shot at an AU!
> 
> I probably won't be posting to it a lot since I'll be working on the Supernatural Rewrite and a new semester is starting so... Think of it as a side project. I'll try to update when I can :)

King Chuck held his head in his hands. The king exhaled deeply, his servants watching him warily. Their leader was normally a calm, mellow man, but his well built exterior was beginning to crumble.

“Bring me my daughter,” the king simply ordered, his voice drained. He looked up at his many servants, waiting for one of them to move with tired eyes.

“Right away, your majesty,” one of the servants mumbled then scurried off to fetch the Princess from her chambers.

Sir Bobby Singer sat across from the king, hands folded in front of him on the grand table. He leaned forward in his chair, observing his old friend with a knowing look. “You do realize what we must do, my king?”

“Yes,” the king replied somberly, head bobbing slowly. “She won’t like it but it needs to be done.”

His closest friend and right-hand man nodded once, resting back in his chair. The King and ex-kight spoke without speaking, their glances communicating the unsaid.

“You called, Dad?”

Her voice brought a smile to his face, but it fell when he remembered why he beckoned her here.

“Y/n, Princess,” Chuck stood up from his chair and smoothed down his robes. “We need to talk.”

“Oh, well, that’s never good,” the young princess joked as she walked over to her father. “What’s up?”

King Chuck ignored his daughter’s informal choice of words and sighed, preparing himself for the argument that he expected to unfold. “Lucifer intends on attacking our kingdom. I need you to get as far away from our borders as possible, for your safety.”

“For my safety?” Y/n repeated disgustedly. “I am perfectly safe here, ruling at your side. Besides, it would be foolish of you to send me away. I have terrific strategy ideas, Bobby even said so himself!”

Bobby’s face fell, cursing his past self for praising the intelligent princess. He should've known that it would come back to bite him in the ass.

“And what of our people’s safety? You’re going to need all the help you can get to maintain order among the villagers and to keep them out of harm’s way,” the princess continued, gesturing wildly with her arms. “So, no, father, I will not be going anywhere until you give me a damn good reason why!”

“Hush, child, and let me finish,” Chuck snapped. “I’m sending you on a mission.”

Y/n’s face light up with excitement. “A mission? You want me to spy on opposing kingdoms?”

“Oh, God, no,” Chuck replied, shaking his head. “No, your mission is to find a prince worthy of your hand in marriage.”

The princess blinked, the bursted into fits of laughter. She waited for her father to join her merriment, but he never chuckled nor smiled for that matter. “You can’t be serious.” King Chuck nodded. “No way! You said you would let me marry out of love!”

“Which is why you’re going to find the prince yourself,” Chuck retorted.

Y/n exhaled through her nose sharply, closing her eyes in attempt to calm herself down. “That is one bullshit excuse, father,” the stubborn princess stated flatly.

“Language, Y/n!” her father snapped, his face reddening from rage. “Have you forgotten who we are talking about? Lucifer! He wants to capture you and use you as leverage against me. I have lost your mother to him before, and I do not plan on losing you as well.”

Y/n’s face dropped, her arms hanging at her sides as her whole body deflated. How could she have been so stupid? So insensitive?

The king sighed, dragging a hand over his face. “Bobby, tell her the rest of the details. I’ll be in my chambers.” Chuck left the dining hall, a few servants following him out of the room, the large doors booming behind them.

**[YOUR POV]**

You pulled out one of the chairs from the table and took a seat, suddenly feeling the need to sit down. Your head hung, your hands suddenly very interesting. Bobby watched you carefully for a moment before he spoke.

The old man, who you considered family, sighed. “I know you don’t like it. Believe me, we don’t either,” Bobby said, referring to him and your father. “I’d much rather have you stay here where I can keep an eye on you myself, but that would just put you in more danger. Which is why I’m sending Knight Winchester with you. He’s young--about your age, actually--but I’d trust him with my life. Dean has a map with all the kingdoms your father marked out for you to visit. You leave tomorrow morning. Garth has already been informed and prepares your horse as we speak.”

You nodded, taking in the information halfheartedly. You would be reminded of your journey in the morning, anyway.

“Jessica should be in your chambers waiting for you. She will help you pack your things,” Bobby concluded. He reached for your hand from across the table; you took his hand and he gave your’s a squeeze. “Everything is going to be just fine, Princess.”

You swallowed, and gave the old man a smile. “I know,” you replied, nodding earnestly.

Bobby returned your smile and released your hand of his grip. “Go get some sleep, kid. You have a long journey ahead of you.”

You stood up from the chair and wished Sir Bobby goodnight. Your newer servant, Silvia, escorted you to your room where Jessica was waiting for you, just as Bobby said.

“Thank you, Silvia,” you whispered to the girl. She curtsied, spewed out a goodnight, and scurried off to the servants’ quarters. Her shyness brought a temporary smile to your face, but the news you were just made aware of crashed your party when your gaze fell on a teary-eyed Jess.

You ran into her arms, your chest aching as your suppressed a sob. Jessica, on the other hand, embraced her emotions and freely expressed them, a body wracking sob shaking the both of you as hugged.

“I can’t believe they’re sending you away!” She grabbed your arms, pulling away so she could look at your face. “And to find a husband during a war? Has your dad gone mad?” Jessica exclaimed, wiping stray tears from her cheeks.

“Quiet, Jess,” you warned your friend, “someone might hear you.” Jessica rolled her eyes, but you knew she understood. You sighed and pulled her to your bed, the two of you sitting on the edge. “Believe me, I’m mad, too, but I understand why my father wants me to go.”

“Yes, I know.” Jessica eyed you for a minute before adding a comment you didn’t expect to hear from her. “I don’t think searching for a hot prince will be that bad though,” your friend mumbled, wiping her stuffy nose.

“Jessica,” you scoffed, “you just expressed how insane my father is for sending me on a love quest!”

“Yeah, but now that I’ve considered the pros and cons, I think looking for a husband in such pressing times will add a… sexy, dangerous factor,” Jessica admitted scandalously.  

You laughed, your head tilting back, “You’re crazy, Jess.”

“But you love me,” Jessica replied, cocking her eyebrow confidently.

“True,” you said as your laughter subsided. You gazed at your friend sadly. “How am I going to spend a month away from you?”

“A month! That’s how long you’ll be gone?” Jessica asked, her voice higher than usual in fear.

You shrugged. “More or less,” you said with a frown.

Jessica sighed, sucking on the inside of her cheek as she thought. “I’ve got it!” She ran over to your large dresser and pulled out a box you didn’t know was in there.

“Um, what is that?” you questioned, rising from the bed to get a better look.

“A box of my things,” Jessica explained over her shoulder. “I keep things I don’t want the other servants going through in here. I hope you don’t mind,” she added sheepishly.

You waved your hand, dismissing it. Jessica grinned and pulled out a bundle of parchment paper, the thick stack tied together with corse string. “My mother gave these to me for my birthday when I went through my sketching phase,” Jessica said as her fingers thumbled with the string’s end. “God knows I haven’t touched these papers since I was 16. I want you to take them with you so you can write to me.”

“Jessica, I can’t take those from you,” you said, shaking your head.

“Did you not hear what I just said? I don’t plan on using these parchments anytime soon, so what’s better than to make use of them?” Jessica argued. “Take them, Y/n. Oh, and this pencil,” Jessica added, slipping a wooden pencil in the knot of the string.

You sighed and took the stack of papers from Jessica, a pleased smile on her face. “Thank you, Jess.”

“Now you just have to promise that you’ll write to me everyday,” Jessica said, pointing a finger at you. “Think of me as your own personal, living diary.”

You chuckled, “Sure. We’ll call it that.” You gestured at your closet. “Now are you going to help me pack or what?”

~~~

Later that night, after Jessica packed you a few gowns, extra undergarments, and riding gear, she talked to you as you changed into your nightgown.

“Who did Bobby say is escorting you around the country?” Jessica asked as she braided your hair.

“Knight Winchester,” you answered, watching her hands weave your hair through the mirror.

“Winchester? As in Dean Winchester?” Jessica asked dumbfounded.

“Yes, that’s the one,” you replied, wondering why Jessica was so shocked.

“Oh my god,” Jessica mumbled as she looked at your blank expression in the mirror. “You’ve never met Dean before have you?”

Your face scrunched up in confusion. “No?”

“Well, no wonder you’re not excited about your journey!” Jessica cried, tying the bottom of the braid. “You won’t have to worry about not seeing any breathtaking views ‘cause Dean’s got you covered.”

“Jessica,” you gasped, giggling at her change of mood. Just an hour before, the two of you were crying and now here you were giggling like young girls.

“What? The man is good looking! His brother though,” Jessica paused, “that boy is mine,” she said deviously. You smiled and shook your head. “In all seriousness, Y/n, Dean is a great guy. I think you’ll like him. You’re in good hands.”

“I’m glad,” you said, staring at yourself in the mirror. You sighed and looked at Jessica. “We should get to bed if we’re going to wake up on time.”

Jessica exhaled sharply. “I guess you’re right.”

“I’m always right.”

“Don’t flatter yourself, Princess.”

You stuck your tongue out at your friend, the two of your giggling once more. Jessica walked over to the door, stopping in the doorway. She turned over her shoulder, giving you a wink and wished you a goodnight.

It amazed you how your best friend could turn any bad situation into a good one. How were you going to be able to last a month without her? Before tears could spill from your eyes, there was a knock at your door.

“Come in,” you called out, attempting to keep your voice level.

The door opened, your father peeking his head through the crack. You turned away from him, sitting on your bed and crossing your arms; you weren’t ready to admit to him that you understood his fears. You were still upset that he didn’t think you’d be able to handle yourself. He frowned at your stubborn behavior and looked around the room before entering.

He sat next to you on the bed, but you refused to meet his eyes. Chuck sighed, looking at the floor. “Y/n, I…” He stopped, trying to find the right words to explain the clutter going on his head. He chuckled, his laughter tired and broken. “Your mother normally handled our disagreements,” the king said, sadly.

You looked at him then and saw how worn out he appeared. You couldn’t stay mad at your dad, it was impossible. Your bottom lip quivered, hot tears sat in your tear ducts waiting to be released. You let out the sob you had been holding in all night and wrapped your arms around your father’s neck, pulling him into a hug. He hugged you back, pulling you closer to him, crying silently into your hair.

~~~

The next morning, Jessica and Silvia woke you up early and dressed you in a simple tunic and kirtle over your undergarments, paired with leather riding boots. Jessica rebraided your hair, saying the previous one was too loose, but you knew she was just stalling for time, and you were grateful for that. When she finished braiding your hair, she packed the brush in your bag, and sighed.

“I’ll bring her to the stables, Silvia,” Jessica told the other servant.

“Are you sure? I can-”

“I’m sure. Thanks,” Jessica replied curtly. Silvia closed her mouth instantly, mumbled an apology and rushed out of the room.

“Gosh, Jess, you nearly bit her head clean off,” you murmured as your bedroom door closed.

Jessica shrugged. “That girl can’t take a hint.”

The two of you walked to the stables exchanging small talk as your time together winded down. “I packed you a pair of slippers for you to wear with your gowns, an extra chemise if the one you’re wearing gets dirty, an extra tunic and kirtle and of course that brush and the papers,” Jessica rambled on, listing off the things in your bag. “I also snuck you some bread from the kitchen.”

“When did you do that?” you asked, genuinely curious.

“This morning while I was talking to Jody. She was so caught up with scolding a dishwasher boy she didn’t even notice me sneak the whole loaf,” your friend expanded. Jessica released a shaky breath as you entered the stables, Garth waving the two of you over.

“Morning, Princess Y/n, Jessica,” Garth greeted you in his usual chipper voice. Your horse, Caspen, nickered as you approached, his head lowered. You stroked his slate-grey muzzle, his warm exhale hitting your hands.

“Good morning, Garth,” you replied, turning to face the stable boy. “Is Caspen all ready to go?”

“Yes, ma’am,” Garth replied with a nod and a smile. Jessica handed him your bag for him to strap to Caspen’s saddle. “There’s some extra carrots and hay in the pack,” Garth said, nodding to the pack on the other side of Caspen.

“Thank you, Garth,” you said, checking the pack yourself. Sure enough, there was extra food and a small mole-skin canteen of water for your horse.

“Where’s Dean?” Jessica asked, looking around the empty stable, not including the other horses in their stalls.

“I’m pretty sure he’s talking with Sir Bobby and King Chuck. He stopped by earlier to prepare his horse,” Chuck replied, double checking the leather straps securing the bags to Caspen’s back.

“He readied his horse himself?” you asked, shock evident in your voice. Normally, the knights left Garth to take care of the horses after a patrol or training.

Garth nodded. “He loves his horse--treats her like family. She was given to him by his father.”

You nodded, your curiosity peaking. Wondered why you never heard of Dean before or seen him around. Bobby did say he was younger, so maybe he was a new recruit?

“Y/n!” Your father stood at the entrance of the stable next to Bobby and a young man with a black mare. “I didn’t think you would be here so early,” Chuck said as he and the other men walked over to you and your friends.

“You said I leave in the morning, so,” you lifted your arms at your side, “here I am.”

“I see,” Chuck replied. You glanced between him and the handsome man leading the mare. “Oh, this is Knight Dean Winchester. As you already know, he will be escorting you around the kingdoms.”

You nodded and gave the boy a smile, relieved that you were traveling with someone more your age and, from the looks of it, nice. Dean returned your smile with his own tight smile, anxious to leave.

“Well,” Jessica sighed, pushing a strand of hair behind her ear, “I should let you go.”

You tried your hardest not to cry, a whimper upon your lips as you pulled your friend into a hug. “I’m going to miss you, Jess,” you whispered into her hair.

Jessica sniffs. “I’ll miss you, too. Remember to write,” she said firmly though her voice was shaking and her eyes brimmed with tears.

“I will,” you reassure her, pulling away from the embrace. Your friend wiped at her eyes and quickly dismissed herself, not wanting to embarrass herself in front of such powerful men.

You turned around, smoothing down your dress, and looked at your father. A crumpled smile was on your face and tears threatened to spill from your eyes. This whole plan shook your world, turned it upside down and inside out. King Chuck enveloped you in his arms, his robes surrounding the two of you. He rubbed your back soothingly, hushing you in your ear, hot tears rolling down your cheeks. You sniffle, constructing a tough exterior for your father, for Bobby, for Dean, Jessica, and the kingdom.

“Are you ready to go?” your father asked you hesitantly, his blue eyes searching your e/c ones, his hands cupping your face.

You nodded, grabbing his hands and putting them on his chest. You released a shake breath and wiped at your eyes. You mounted Caspen, your father offering his hand for balance. You didn’t need it, but you took it, putting your father’s loving gestures to memory. Dean mounted his mare, waiting politely.

“Be brave, dad,” you told him, looking down at your father and Bobby.

“You too, kid,” Bobby remarked with a sad, but proud smirk.

“Y/n,” you father said seriously, “stay safe.”

“I know,” you replied. You looked at Dean who waited for your okay. You nodded, and he clicked at his mare, the black beauty breaking out in a gallop. You squeezed Caspen’s sides with your legs, Caspen quickly catching up to Dean and his mare. The horses matched each other’s pace, Caspen just a tail to the side of the black mare. You rode through the village, waving to those that watched with confused gazes, and into the forest. You looked over your shoulder, stealing a last glimpse at your home knowing it would be a long while until you saw it again. 


End file.
